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Enantioselective Dearomatization of Naphthol Derivatives with Allylic Alcohols by Cooperative Iridium and Brønsted Acid Catalysis.
Angew Chem Int Ed Engl. 2017 03 13; 56(12):3242-3246.AC

Abstract

The combination of a transition-metal catalyst and organocatalyst was designed to achieve a highly enantioselective system for the allylic dearomatization reaction of naphthols with racemic secondary allylic alcohols. The desired β-naphthalenones, bearing an all-carbon quaternary center, were obtained in good yields with high chemo- and enantioselectivities. The cooperative catalytic system, involving a chiral iridium complex and phosphoric acid, provided measurable improvements in yields, and chemo- and enantioselectivities relative to single-catalyst systems. Control experiments indicated that the chiral iridium complex functions as a key species in the control of the absolute configuration, thus enabling the formation of both β-naphthalenone enantiomers by simply employing opposite enantiomeric ligands.

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Publisher Full Text (DOI)

Authors+Show Affiliations

College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, 310036, China.

College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, 310036, China.

College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, 310036, China.

College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, 310036, China.

College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, 310036, China.

Pub Type(s)

Journal Article

Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

28194912

Citation

Shen, Dan, et al. "Enantioselective Dearomatization of Naphthol Derivatives With Allylic Alcohols By Cooperative Iridium and Brønsted Acid Catalysis." Angewandte Chemie (International Ed. in English), vol. 56, no. 12, 2017, pp. 3242-3246.

Shen D, Chen Q, Yan P, et al. Enantioselective Dearomatization of Naphthol Derivatives with Allylic Alcohols by Cooperative Iridium and Brønsted Acid Catalysis. Angew Chem Int Ed Engl. 2017;56(12):3242-3246.

Shen, D., Chen, Q., Yan, P., Zeng, X., & Zhong, G. (2017). Enantioselective Dearomatization of Naphthol Derivatives with Allylic Alcohols by Cooperative Iridium and Brønsted Acid Catalysis. Angewandte Chemie (International Ed. in English), 56(12), 3242-3246. https://doi.org/10.1002/anie.201609693

Shen D, et al. Enantioselective Dearomatization of Naphthol Derivatives With Allylic Alcohols By Cooperative Iridium and Brønsted Acid Catalysis. Angew Chem Int Ed Engl. 2017 03 13;56(12):3242-3246. PubMed PMID: 28194912.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Enantioselective Dearomatization of Naphthol Derivatives with Allylic Alcohols by Cooperative Iridium and Brønsted Acid Catalysis. AU - Shen,Dan, AU - Chen,Qiliang, AU - Yan,Peipei, AU - Zeng,Xiaofei, AU - Zhong,Guofu, Y1 - 2017/02/14/ PY - 2016/10/03/received PY - 2017/01/12/revised PY - 2017/2/15/pubmed PY - 2017/2/15/medline PY - 2017/2/15/entrez KW - allylic compounds KW - enantioselectivities KW - iridium KW - organocatalysis KW - synthetic methods SP - 3242 EP - 3246 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 56 IS - 12 N2 - The combination of a transition-metal catalyst and organocatalyst was designed to achieve a highly enantioselective system for the allylic dearomatization reaction of naphthols with racemic secondary allylic alcohols. The desired β-naphthalenones, bearing an all-carbon quaternary center, were obtained in good yields with high chemo- and enantioselectivities. The cooperative catalytic system, involving a chiral iridium complex and phosphoric acid, provided measurable improvements in yields, and chemo- and enantioselectivities relative to single-catalyst systems. Control experiments indicated that the chiral iridium complex functions as a key species in the control of the absolute configuration, thus enabling the formation of both β-naphthalenone enantiomers by simply employing opposite enantiomeric ligands. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/28194912/Enantioselective_Dearomatization_of_Naphthol_Derivatives_with_Allylic_Alcohols_by_Cooperative_Iridium_and_Brønsted_Acid_Catalysis_ L2 - https://doi.org/10.1002/anie.201609693 DB - PRIME DP - Unbound Medicine ER -